Did Kendall Jenner and Harry Styles Dating? Everything You Need To Know!

Did Kendall Jenner and Harry Styles Dating: Kendall Jenner, of Keeping Up with the Kardashians & Harry Styles, of One Direction, were repeatedly connected romantically from 2013 until 2019. Even though they never came out & said they were dating, the model & the singer have a long history together that includes excursions on Ellen DeGeneres' boat & New Year's Eve ski outings.

When the former One Direction member filled in for James Corden as host of The Late Late Show in December 2019, Jenner & Styles enjoyed a memorable “meal” together. During their appearance, the two appeared to be old friends as they participated in Corden's “Spill Your Guts or Fill Your Guts” game. Here's a look at how long Harry Styles has been dating Kendall Jenner, from their first date to the day they spilled their guts on late-night TV.

When Did Kendall Jenner Date Harry Styles?

In 2013, after being introduced by their respective managers, Kendall and Harry were first seen kissing. Reconciliation rumors surfaced two years later after they were spotted together on a yacht in Anguilla.

Did Kendall Jenner and Harry Styles Dating

They reportedly broke up shortly thereafter. While they never came out and said they were dating, rumors have it that they were seeing one other on and off for years. Both at 2019 Met Gala and subsequently on The Late Late Show with James Corden, Harry and Kendall reconnected with one another.

Read More – Who Is Jason Nash Dating 2022? Did He Make Shocking Revelations?

Kendall & Harry Styles' Relationship Timeline


After his breakup with Taylor Swift earlier that year, he and Craig were spotted leaving Craig's restaurant in West Hollywood in Styles' car for supper. Both sides were quick to dispel any romantic speculation that may have arisen from the encounter.

An insider told PEOPLE, “They're simply pals,” and Kendall tweeted that she was happily single. In the future, on December 1, 2014, the duo was spotted together at the British Fashion Awards alongside mutual friend Cara Delevingne, once again fueling speculation of romantic tensions between them.


Styles & Jenner were observed snow sporting on New Year's Day, 2014, in Mammoth, California. The two were spotted staying at a property with several other people, however, they appeared to be a couple. After the trip, a witness reportedly told PEOPLE, “Harry went skiing & Kendall rode a snowboard.

To put it simply, they made a cute couple. Lots of winking & smiling occurred.” People also commented on how “gentlemanly” Harry was by saying things like, “He even volunteered to carry Kendall's snowboard to the ski lift.” Absolutely breathtaking winter scenery!


On January 1, 2014, Styles and Jenner were spotted snow-sporting in Mammoth, California. It appeared that the two were a couple when they were seen at a rental house where several others also were staying. An eyewitness reportedly told PEOPLE after the vacation, “Kendall rode a snowboard, and Harry went skiing.Did Kendall Jenner and Harry Styles Dating

Simplistically put, they were adorable together. Huge amounts of smiling and winking took place.” The “gentlemanliness” of Harry was remarked upon by onlookers, who noted that he “even volunteered to carry Kendall's snowboard to the ski lift.” Fantastic winter landscapes, for sure.


Celebrity reunions during fashion's biggest night are nothing new, but when Kendall & Harry were photographed chatting inside the event in May 2019, it sent a clear message. They continued their evening together. A source at the time told that the two were not dating & that Kendall was still seeing her ex-boyfriend, Ben Simmons. According to our insider, “Harry was her first serious relationship, so there is a lot of history there,” but ultimately, Harry & Kendall are simply friends despite their long past together.

Who Is Kendall Jenner Dating Now?

When basketball star Devin Booker & model Kendall Jenner were spotted together in early 2020 outside a rest stop in Sedona, Arizona, rumors began to circulate. After some time, they admitted that they were dating, and they've been together off and on ever since.

Read More – Who Is Savannah Chrisley Dating? Is She Still Dating Nic Kerdiles?

Who Is Harry Styles Dating?

Reportedly, Olivia Wilde & Harry Styles started dating in the first month of 2021. The rumors of Kendall Jenner & Devin Booker's relationship are true. Olivia directed & performed with Harry in the film Don't Worry Darling & the experience started a romance between the two. In addition to Harry, Olivia & co-star Jason Sudeikis are in the midst of a heated custody fight following their recent separation.

I hope you found this article interesting. The website provides up-to-date articles & news. Everything you need to know is right here. Don’t forget to give your feedback in the comment section & don’t forget to bookmark our website Michigansportszone for more such articles.